2024
C–H Activation and Sequential Addition to Dienes and Imines: Synthesis of Amines with β‑Quaternary Centers and Mechanistic Studies on the Complex Interplay Between the Catalyst and Three Reactants
Goodner R, Brandes D, Morais G, Tao Q, Tassone J, Mercado B, Chen S, Ellman J. C–H Activation and Sequential Addition to Dienes and Imines: Synthesis of Amines with β‑Quaternary Centers and Mechanistic Studies on the Complex Interplay Between the Catalyst and Three Reactants. ACS Catalysis 2024, 18124-18133. DOI: 10.1021/acscatal.4c05866.Peer-Reviewed Original ResearchRhodacycle intermediateCatalytic cycleX-ray structure analysisDensity functional theory calculationsC-H activationDeuterium labeling studiesSynthesis of aminesTransition state structuresFunctional theory calculationsFormaldimine precursorsEthyl glyoxylateHigh diastereoselectivityN-CbzNitrogen substituentQuaternary centerAlkyl substituentsAlkyl sulfonamidesC-HTheory calculationsRhodacycleState structuresCarbon sitesDienesX-rayMechanistic studiesSynthesis of α‑Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates
Yeo J, Tassone J, Ellman J. Synthesis of α‑Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates. Organic Letters 2024, 26: 9769-9774. PMID: 39481088, PMCID: PMC11578270, DOI: 10.1021/acs.orglett.4c03740.Peer-Reviewed Original ResearchSynthesis of Monodehydro-Diketopiperazines Enabled by Cp*Rh(III)-Catalyzed Amine-Directed N–H Functionalization
Molas J, Poag E, Ellman J. Synthesis of Monodehydro-Diketopiperazines Enabled by Cp*Rh(III)-Catalyzed Amine-Directed N–H Functionalization. Organic Letters 2024, 26: 8527-8531. PMID: 39332014, PMCID: PMC11512471, DOI: 10.1021/acs.orglett.4c03105.Peer-Reviewed Original ResearchEnantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie 2024, 136 DOI: 10.1002/ange.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystEnantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie International Edition 2024, 63: e202408820. PMID: 39058627, PMCID: PMC11514311, DOI: 10.1002/anie.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystDisulfide Tethering to Map Small Molecule Binding Sites Transcriptome-wide
Moon M, Vock I, Streit A, Connor L, Senkina J, Ellman J, Simon M. Disulfide Tethering to Map Small Molecule Binding Sites Transcriptome-wide. ACS Chemical Biology 2024, 19: 2081-2086. PMID: 39192734, DOI: 10.1021/acschembio.4c00538.Peer-Reviewed Original ResearchCytochrome c oxidase 1Binding sitesRNA-small molecule interactionsPotential binding sitesTranscriptome-wide screeningSmall molecule disulfideSpinal muscular atrophyCellular RNARNA sitesTarget RNAMetabolic labelingSmall molecule bindingRNADisulfide analoguesLead moleculesMolecule bindingTranscriptomeFDA-approved drugsStructural probesMolecule interactionsCovalent attachmentDisulfide tetherThermodynamic propertiesTreat spinal muscular atrophyDisulfideRh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality
Patel S, Greenwood N, Mercado B, Ellman J. Rh(II)-Catalyzed Enantioselective S‑Alkylation of Sulfenamides with Acceptor–Acceptor Diazo Compounds Enables the Synthesis of Sulfoximines Displaying Diverse Functionality. Organic Letters 2024, 26: 6295-6300. PMID: 39004842, PMCID: PMC11292377, DOI: 10.1021/acs.orglett.4c02402.Peer-Reviewed Original ResearchCopper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines
Chu D, Zoll A, Ellman J. Copper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines. Organic Letters 2024, 26: 4803-4807. PMID: 38810982, PMCID: PMC11195447, DOI: 10.1021/acs.orglett.4c01634.Peer-Reviewed Original ResearchCorrection to “Catalytic Enantioselective Sulfur Alkylation of Sulfenamides for the Asymmetric Synthesis of Sulfoximines”
Greenwood N, Champlin A, Ellman J. Correction to “Catalytic Enantioselective Sulfur Alkylation of Sulfenamides for the Asymmetric Synthesis of Sulfoximines”. Journal Of The American Chemical Society 2024, 146: 5712-5712. PMID: 38364827, DOI: 10.1021/jacs.4c00239.Peer-Reviewed Original Research
2023
Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines
Vargas-Rivera M, Liu A, Ellman J. Visible-Light-Mediated, Diastereoselective Epimerization of Exocyclic Amines. Organic Letters 2023, 25: 9197-9201. PMID: 38114418, PMCID: PMC10771010, DOI: 10.1021/acs.orglett.3c03801.Peer-Reviewed Original ResearchSynthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie International Edition 2023, 63: e202315701. PMID: 38015869, PMCID: PMC10813656, DOI: 10.1002/anie.202315701.Peer-Reviewed Original ResearchS bond formationOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidSynthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie 2023, 136 DOI: 10.1002/ange.202315701.Peer-Reviewed Original ResearchOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidStyrene